


Dirty Money

by Merwood



Category: Teen Wolf (TV)
Genre: Bottom Derek, Explicit Sexual Content, M/M, Polyamory, Prostitute Derek, Prostitution, Top Jackson Whittemore
Language: English
Status: In-Progress
Published: 2014-05-23
Updated: 2014-05-23
Packaged: 2018-01-26 05:38:20
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 9,068
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1676702
Author URL: https://archiveofourown.org/users/Merwood/pseuds/Merwood
Summary: <blockquote class="userstuff">
              <p>Derek's been trading sex for cash for six years.  Ever since he lost everything, his house, his family, he's even lost his only friend and mentor; the kid who helped him settle into his new life as a prostitute.  He's getting older and the old perverts who like 'em young are losing interest.  Tonight Derek gets picked up by Jackson and is about to experience one of the most humiliating nights of his life and he's also going to get an offer that just might be to good to be true.</p>
            </blockquote>





	Dirty Money

**Author's Note:**

> Bit of a warning, dubious consent is a prominent theme in this story, as most prostitutes technically consent they’re doing it out of necessity not because they actually want to. There will be mentions of past under age sex but I won't be going into much detail about it other then knowing that it occured.
> 
> Also, this story is going to deal with a fair bit of sexual themes. Jackson’s young, rich and not shy about sex; he gets a little kinky. This story is also going focus on a polyamory relationship. With for those who don’t know what that is, its being in love with or dating more than one person at a time(all parties are aware, not cheating). So instead of the usual person A ends up with person B at the end its going to be Person A, B and C all decide to date.(Might be more than 3, depends if I decide to write a sequel or a longer fic)
> 
> Lastly for those of you who read stories specifically for a certain character to top or bottom I’ll let you know that Jackson will be the primary top in this fic, but overall everyone is going to switch it up.
> 
> No beta, all mistakes are my own.(I changed the title and summary because I felt it made the story come off lighter and too vague.)

Derek twirls the old metal nail file around between his fingers trying to distract himself from the chill of the night air. Its still early spring and without the suns warmth the too tight black T-shirt and skin tight pants offer little protection against the elements. Normally he would have given up by now but its coming up to the end of the month and bills are due; he’s got three days to make three-fifty and that’s not counting if he wants to eat. Normally five-hundred means he’s had a really good week, he’s more than a little worried about making his rent.

He misses the days when he could pull a grand a week, back when he was sixteen and still had a twinky build, slim and young looking with no facial hair. Far too young looking for the age of the men who were picking him up. Sixteen had been his peak, when he had worked long enough to learn how much dirty old pervs would pay for him and when he had the perfect build to attract them. Though he owed a lot to Manny for teaching him the ropes. The kid was two years younger than Derek but had been selling himself almost a year prior. Of course that golden year where he was able to make ends meet didn’t last. He soon hit six feet and developed broad shoulders and perpetual afternoon shadow.

After that his client base steadily fizzled out and changed. Instead of getting the old perverts who liked them young and easily cowed he started attracting the chubby older guys who wanted a big jock type to fuck them into a mattress. Derek preferred that but there simply weren’t enough johns who wanted to get fucked to pay the bills.

He wished Manny were still around, at least he would’ve shared a corner with him so that they could share body heat. In the six years since Derek had been selling himself Manny had been his only friend and somewhat of a mentor; which looking back is almost ridiculous considering Derek had been two years older than him.

Derek squeezed the file tightly into his palm. He hated thinking about Manny the man - no boy - he was only seventeen when he died. At least Derek assumed he died, after not seeing Manny for over a week he had asked around and found out the last time anyone saw him he drove away with a john in some expensive muscle car. Now three years later and still no word from him. Derek knows the score for people like them; suicide, overdose or murder are the three most common deaths in their line of work. He’d sure missing is probably the number one, but no one ever notices when one of them disappear. Derek’s got six years under his belt and Manny was the only one he’d ever noticed when he stopped showing up for work.

A sharp stinging in his palm causes his hand to flinch away of reflex and the sound of metal bouncing off concrete echo’s throughout the near vacant street corner he’s been freezing his ass off on. He checks his palm and there is a very small trickle of blood from where he must have punctured the skin from the nail file. He sucks on the wound and bends over to pick up the file.

The sudden flash of lights blinds him momentarily as he hears the sound of a car pulling up beside him. He stands up and gives himself a moment to put on his façade as he tucks the file away safely into his side pocket. Convincing balding older men who are way to much over weight that there’s no one he’d rather fuck takes some acting and a lot of imagination for the deed itself.

He goes to lean in the window so he can talk to the john when he notices the car is a fricken Porsche. He’s seen some half decent cars come by but one of this calibre is rarity and he tries not to get his hopes up to much because this guy is definitely going to have money to burn.

The passenger side door pops open and Derek jumps in. The john’s clearly decide he wants Derek for the night so he’s not about to argue. Only the second his ass hit’s the chair and he glances over at the driver he’s more than a little shocked by what he sees.

The john is young, Derek’s not even sure if he’s legal; which probably means he’s in the closet. He’s got high cheek bones and perfect skin. His hair looks light brown which borders on blonde and the guy seems to be in pretty good shape. Rich, young and good looking; Derek wants to punch his face on principle and most definitely not the type of guy Derek has become accustom to being picked up by.

“How much?” The boy asks as he pulls away from the curb and begins driving.

Derek’s about to answer when he stops himself. Rich, attractive kid who he can probably charge two, maybe three times his regular price seems to good to be true. He looks really young but Derek’s not about to take a chance that this guy is actually a cop, or working with them. He’s about to ask when he the john pulls something out of the inside pocket of his jacket and a moment later something plops into his lap.

“Relax, I’m not a cop.” The boy says. Derek looks down and picks up the California State License that the guy tossed at him. He examines it and it looks legit, not that he‘s an expert by any means; it reads Jackson Whittemore, states his eye and hair colour along with height and weight as well as date of birth. Nineteen, three years younger than himself but at least he’s legal. The licence also shows his home address and Derek can’t help thinking this guy is either pretty dumb or its some sort of setup.

“We gonna talk shop or you plannin’ on giving me a freebee?” Jackson’s voice pulls Derek back to the present. He gives the guy a dubious once over and decides to take the risk, he really needs the money and as long as its just them he’s confident he can take him.

“Two-Hundred for a blow job and five-hundred for a fuck.” Its almost five times the amount of what he normally asks but Manny always told him when you know someone’s rich to always ask for at least triple. Nine times out of ten they won’t even blink an eye and Derek’s got this kid pegged as a over privileged trust-fund casualty who doesn’t think twice about the average worth of a street hooker.

Jackson has the nerve to snort at Derek as he glances over and gives him a cocky, knowing smirk, that unsettles Derek.

“How about you tell me your real prices before I Turn around and pick up that skinny kid across the street who will probably let me do just about anything to him for a fifty.”

“Forty for head, hundred for a fuck.” Derek grinds out between clenched teeth all the while digging his nails into his palms. He thought about trying for double his normal price, but Derek really can’t afford to lose this guy even if he’s a little cheap. 

After selling himself for so long he’d come to accept that anyone could have a go at him for a price, and he’d slept with some really sleazy and unattractive men over the years. Ugly, he can handle. Johns with weird fetishes, whatever. But stupidly attractive rich brats with condescending attitudes who didn’t know how lucky they had it? He wasn’t sure if what little was left of his pride could handle this kid.

“How about eighty for a fuck, and if you're any good and we go a second round I’ll make it one-fifty.” Jackson asks without looking over and Derek doesn’t think it sounds much like a question so much as his counter offer..

Derek wants to tell him to go to hell simply because he already hates the kid but he knows this will be his only client tonight and the chance at one-fifty is better then nothing.

“Fine.” Derek growls.

“You know, for a whore your customer service is shit.” Jackson’s tone sounds matter-of-fact and not insulting, Derek can’t help but snort at the comment.

“You’re picking up a stranger for sex not shopping at Wal-mart.” Derek says as he passes Jackson back his license. “You know, giving me your real name isn’t overly smart, what we’re about to do isn’t exactly legal. How do you know I won’t blackmail you?”

“Pretty sure if you were aiming for blackmail you wouldn’t have mentioned it until after you had your money.” Jackson says as he tucks his license back into his jacket pocket. It’s a varsity sport coat, Derek assumes for whatever sport he played or plays in high school. “Anyway, I’m nineteen. Not exactly worried about my rep. I suppose you could find me on facebook and tell all the kids I no longer talk to from high school.”

Derek concedes Jackson has a point. He won’t bother mentioning calling the police because he already knows they’ll take Jackson’s word over his and he suspects Jackson knows that too.

“So what’s your name?” Jackson asks.

“Pete.” Derek replies without hesitating. He made the mistake of using his real name in the beginning, luckily Manny had found him before the first time he got picked up by the cops for soliciting. He’s not sure what it says about him that he uses his comatose uncles name while whoring, but it was the first that came to mind when Manny had him pick one. Derek never thought to ask Manny if that was his real name.

Derek can tell Jackson doesn’t believe him and Derek is getting a little pissed that this teenage punk can read him so well. Hates that he needs to suck it up if he wants to make rent.

“Well, Pete.” Jackson says with an emphasizes on Pete. “We’re here.”

Derek looks out the window as Jackson turns into the driveway of a large two story home which Derek is fairly certain borders on mansion. Somehow Derek didn’t think even Jackson would take a hooker home to his parents house but can’t understand in what fair universe a nineteen-year-old can afford such a place. He can’t help but wonder why Jackson didn’t just take him back to some hotel.

The front gate is automated so Jackson didn’t even need to get out to open up the driveway gate and the front lawn is immaculate. A healthy green and perfectly cut. The garage door opens and Jackson pulls in and turns off the ignition.

“Welcome to my humble abode.” Jackson says as he jumps out the car, the smirk tells Derek that Jackson knows just how humble his home is not. He climbs out Jackson’s Porsche and ignores the second vehicle. He already has enough reason to hate Jackson and he refuses to let him see just how jealous he is of his life style.

“Hungry, thirsty?” Jackson asks as they enter the kitchen through the adjoined door. Derek says no because he just wants to get this over with and ignores the growling in his stomach. He never spends more time with a john then he absolutely has to. “Thank god, I’m horny as fuck.”

For all the reasons Derek wants to hate Jackson for; strangely he finds Jackson’s forwardness refreshing. Derek doesn’t need to be told he’s special and somehow Jackson doesn’t make him feel like he’s filth, or less than human.

Derek keeps his focus strictly on Jackson’s heels. He doesn’t want to be tempted to try and rob anything, rich folk make the worst enemies and cops tend to bend over backwards for them.

“Close the door behind you.” Jackson says as he enters the first bedroom after they reached the top of the stairs.

Derek does as he’s told and takes a moment to look around the room. It’s a large bedroom, larger than any bedroom he’s ever been in. The bed looks to be about a queen size and is made up nicely with a ridiculous amount of pillows at the head. There is a dresser, desk and all the basic necessities a room should have, complete with a connecting bathroom on one side and what looks like a closet on the other. The rooms setup looks like it came straight out of a catalogue but completely lacks that lived in vibe one would expect from someone’s bedroom.

Jackson’s made himself comfortable on the bed, legs splayed unabashedly wide. His eyes roaming Derek as Derek’s had been the room. Only Jackson’s gaze is far less curious and far more predatory.

“Strip.” Jackson commands. Derek swallows audibly and feels for the first time in years that he might be in over his head. He’s grown far to comfortable with clients who like to be bossed around, like having him in charge.

Derek kicks off his hiking boots and bends over to pull off his socks, tucking each one into the appropriate boot. He grabs the hem of his shirt and pulls it up over his head and discards it to the floor. He can see the outline of the bulge forming in Jackson’s pants as the man shrugs out of his jacket, eyes never leaving Derek’s form.

Derek undoes his belt and quickly unbuttons his fly and shoves his pants to his ankles as he kicks them off. Its not overly sexy, but Derek has yet to find a way that looks sexy when taking off skin tight jeans. Jackson doesn’t seem to mind as he palms himself while he watches Derek step out of them. He’s got his thumbs hooked into the waistband of his boxer briefs when he realizes he’d almost made a rookie mistake.

“Money first.” Derek’s voice comes out shakier then he’d like. Jackson stands up as he reaches into his back pocket for his wallet. Derek can’t help but check out the prominent outline of Jackson’s hard cock through his jeans and inadvertently licks his lips. It’s been a long time since he’s gotten excited about getting to fuck one of his johns, but for all the things Derek dislikes about the man he has yet to find piece of Jackson that he doesn’t want to lick and taste.

“One-hundred.” Jackson’s voice and the sound of crinkling paper makes Derek’s gaze shoot up and he hopes Jackson didn’t notice him staring. Judging by the cocky smirk the teens wearing he wouldn’t hold his breath. Jackson holds the hundred dollar bill up so Derek can confirm and then places it onto the nightstand and then tells Derek to get on with it.

Derek isn’t sure why Jackson haggled the first fuck down to eighty and then offered him the hundred anyway, but Derek suspects he did it just because he knew he could. He’s starting to think he should have called Jackson’s bluff and pushed for the five-hundred.

He pushes his boxers down to his ankles and kicks them over to his pants not bothering to cover his cock and balls from Jackson’s view. Its what guys pick him up for after all, being fucked by a hot large man with a big dick is apparently every bottoms dream. At least that’s what more than half his clients tell him.

Jackson doesn’t say anything for a long time and Derek stands there and lets Jackson have his fill. After an uncomfortably long silence Jackson reaches back into his wallet and pulls out another bill and shows it to Derek. It’s a fifty and Derek is sure he’s not going to like why Jackson is throwing more money at him before he’s even done anything yet.

“I like being bossy in the bedroom.” Jackson says by way of explanation and Derek isn’t exactly sure where this is going and that makes him nervous. “Do what I say when I say with no questions asked and the extra fifty is yours.” Derek is about to say no way because that leaves the window open for so many creepy sex kinks Derek would never touch but Jackson doesn’t give him the chance. “Nothing freaky. No fisting or pissing on you or anything. Simple commands, like what position I’d like you in.”

Derek can work with that if it gets him another fifty. He can handle a little humiliation, he’s been selling himself for six years and as far as he’s concerned it doesn’t get much more humiliating then that. He nods and gives his okay and watches as Jackson adds the fifty to the table.

“Turn around.” Jackson says and Derek obeys. He stands there silently facing the door feeling awkward as Jackson stares at his ass. He flinches when he feels a hand touch his thigh and looks over his shoulder to find Jackson mere inches from his face. The hand moves slowly up his thigh and caresses the mound of his ass.

“You have a perfect ass.” Jackson’s says. Such a simple compliment, nothing profound sounding or worthy of Shakespeare. But the way Jackson says it, the rasp of his voice, the gentle touch of his fingers makes Derek blush and he has to look away from Jackson in hopes he doesn’t notice.

“Bend over, grab your ankles.” Jackson orders and Derek blushes for a completely different reason. He obeys, as odd and embarrassing a request that it is, he’s not about to lose that extra cash.

Derek takes up studying his toes because he’s bent over grabbing his ankles and can feel light breaths ghosting over his ass and doesn’t even want to imagine how close that must mean Jackson is to him.

“It’s a shame you’re a whore, I would have loved to give you a good tongue fucking.” Jackson says between light kisses place at the center of each mound of Derek‘s ass.

Derek flinches at the word but again doesn’t detect any malice meant by Jackson’s comment. He’s getting the impression that Jackson is just tactless and a little bit of a dick.

“Get on the bed on all fours.” Derek moves to follow Jackson’s latest commend when the words sink in and he freezes. Jackson’s weird obsession with his ass and wanting him on all fours means that Jackson clearly wants to be the one fucking Derek and Derek isn’t sure how he feels about that. Getting fucked had always been easier, he could simply not think about anything and wait until whoever was done, but he never really enjoyed it. He’s aware apparently hitting ones prostate can be pleasurable but Derek is pretty sure his isn’t very sensitive because he’s never felt anything other than the feeling of uncomfortably full. Like he’s taking a shit and it cant work out which way its meant to go.

“Is there a problem?” Jackson’s voice brings him back to the present.

“err, no. I just assumed you wanted me to fuck you.” Derek says lamely.

“Why would you think that?” Jackson looks genuinely confused which makes him look almost adorable and Derek almost wants to laugh at the thought.

“Its pretty much the only reason people have picked me up for the last three years.” Derek says it like it should be obvious but if anything Jackson looks even more confused.

“But that ass.” Jackson emphases his point by motioning toward Derek’s backside as though that simple statement should prove his point alone. “How long has it been since you’ve been fucked?”

“A year, maybe a bit longer?” Derek’s not really sure on the exact length of time but he does know its been a very long time since anyone’s taken interest in bending him over.

Jackson looks appalled by the new knowledge and Derek actually does laugh aloud.

“I’ve never really minded, I’d rather top. Getting fucked has never felt very good.” The second the words are out he immediately regrets them because rule number one is to keep the client happy. A happy and well fucked client are much looser on the tips and more likely to pick him up again.

“Don’t worry, I’ll show you how good bottoming can actually be. Now, on the bed. All fours.” Jackson says with a light slap to Derek’s ass.

Derek rolls his eyes but does as requested. He’s lost count of how many johns have promised to rock his world and fell short. He climbs onto the bed near the edge where Jackson indicated where he wanted him. His knees are right on the edge with his feet and shins hanging off the end. He arches his back and sticks his ass out and readies himself to be the wanton whore he’s paid to be.

“God, I can’t wait for you to fuck me with your huge cock. I bet you’ll feel so good inside me.” Derek says in a low husky voice while he inwardly rolls his eyes at his shitty porn talk. After the words are out he feels a little foolish upon remember admitting to Jackson seconds ago that he doesn’t like to bottom.

He wasn’t prepared for the hard stinging smack of his right cheek that he gets in reply and yelps indignantly as he glares over his shoulder at a smirking Jackson.

“No faking, or you won’t get a bonus.” Jackson says as he rubs the now reddened flesh where his hand smacked. “I’m pretty selfish in every aspect in my life except in bed, I‘m quiet generous. I’ll earn every moan and have you begging all on my own.”

Derek really doesn’t care if Jackson is the reincarnation of Casanova himself, he’s dead set on being the most unresponsive fuck of Jackson’s life just to put the cocky little control freak in his place.

“Grab a pillow for your head.” Derek grabs the closest one and plops it down just below his head. He’s not exactly sure why he even needs a pillow for his head when he’s on all fours but Jackson is paying for obedience so he doesn’t question it. When he feels Jackson’s hands between his shoulder blades and pushing down the meaning becomes pretty plain. Derek is just glad he can bury his face in the pillow to hid the scarlet shade his face is turning when finding himself face down ass up on the bed.

“Now reach around and spread your ass cheeks wide for me.” Jackson’s tone is conversational, the same tone he used when telling him to close the door. Derek follows the instructions despite how self-conscious he suddenly feels by doing so. In all his years in his line of work he’s never felt so exposed to a client before and Derek can’t even blame it all on the vulnerable position he’s currently in. Something about Jackson has left him feeling like he’s been at a disadvantage from the start. Like Jackson’s been studying him and leaned his tells and bluffs.

Derek shivers when Jackson’s dry thumb begins to slowly circle his rim. “You look hot like this, spread out waiting to be fucked.” Jackson’s voice has fallen back into that same raspy tone he used to compliment his ass earlier. “How much would it cost to let me fuck you bareback?”

“I don’t do bareback.” Derek instantly replies. Its not true, not completely. He’s never been fucked bareback but at desperate times he’s blown guys without condoms for some extra cash.

“Not even for an extra two-hundred?” Jackson asks, his thumb still making the slow tortuous journey around his rim. Derek’s cock doesn’t seem to remember getting fucked quite the same way his mind does because its started reacting to the ministrations. It could also be that Jackson is ridiculously attractive - which is rare for Derek - or he’s discovered a hidden kink for being humiliated. He’s not sure which possibility he’d prefer but knows he’ll never admit to either.

Derek hesitates before replying because that would put him at three-fifty and he’d be guaranteed to make rent. On the other hand Jackson could give him any number of diseases which could possibly kill him or cost him even more to treat. He can’t risk it, his health has been the one constant for him. Even if statistically speaking he’s far more likely to give Jackson something. He breaths out a shaky no and hates how indecisive he sounds. Fucking strangers without condoms shouldn’t be a hard choice, it should even be a choice.

“How about another three-fifty? Walk home with five-hundred bucks, not bad for a nights work, right? Its my last offer and if you turn it down one-fifty is all you’ll get, no tip no matter how good you are.” Derek’s always prided himself on being able to read clients but he cant get a proper read on Jackson. It doesn’t sound like he really cares which Derek picks, which makes him believe like he’s not bluffing. Three-fifty is a lot of money for him and his rent deadline is cutting it pretty close and it would be nice to not get charged that damn late rent fee for once.

“Fine.” Derek concedes. “Five-hundred, no condom.”

He feels Jackson pull away from him and sees him walk over to the end table while digging through his wallet. He pulls out another three-hundreds and a fifty and shows them to Derek and places them on the pile. When Derek braves himself to glance up and Jackson’s face he’s surprised to see that Jackson doesn’t look happy about getting to fuck Derek raw like he wanted, he actually looks a little sad.

Jackson opens up the end table drawer and digs through and pulls out lube and box that Derek doesn’t get a chance to read and disappears once again to take up position behind Derek.

“Don’t worry, I don’t actually plan of fucking you bareback. I was just curious if you’d let me.” Jackson says as he squirts a bit of lube onto his fingers and rubs it between his fingers and thumb to warm it. “You can keep the money though,” he adds as an after thought.

Derek is sure his face is a colour resembling that of a tomato as he buries it in the pillow feeling equal parts shame and relief. And maybe just a little bit of hate for Jackson for making him feel dirty and desperate all for his own amusement. He won’t cry over it, he hasn’t in years. But for the first time in a long while he finds he needs to hold back the tears. Yeah, he definitely hates Jackson more than a little.

Jackson’s finger is back over the bud of Derek’s entrance and he feels the cool slid of lube as Jackson drizzles a bit down his crack and onto his hole. Jackson slowly slides his index finger in, not much, just enough to push some lube in. The distraction is welcome from the humiliation of moments ago and he starts when a hand gently takes hold of his balls. He forces down the appreciative moan, no way he’ll give Jackson the satisfaction after is little game. Even is the gentle massaging of his balls feels pretty damn good.

Jackson’s hand slides further up his balls and his fingers run painfully slow along the hard shaft of his cock. His cock is fully erect and he has no idea when that happened. They’ve hardly begun, Jackson’s only just got his first finger in. If they continue at this pace Jackson might just get what he wants and reduce him into a quivery mess begging for release.

Derek can feel soft feather light kisses being placed randomly about his ass. Derek tries to find a pattern to distract himself but Jackson doesn’t seem to have one. One to the center of his left cheek, another just above the cleft of his ass. Then back to the left just below his hip followed by one to the right side where is thigh and ass meet. If Derek didn’t know better he’d think Jackson was worshiping his naked body, but buries those thought immediately because he’s a whore after all. People pay them the lowest amount they can get away with to use their body and then walk away. Unless they’re an irritating rich teenager with a pretty face who gets off on over paying for the privilege of adding some humiliation. He’d tell Jackson the jokes on him, that every time he excepts money for sex its humiliating, so the extra stuff means nothing. The truth is Jackson has a gift, he’s only known the guy for a couple of hours and already he knows its an encounter he’ll never forget. No one before has ever made Derek feel so simultaneously accepted and humiliated and so completely unnerved.

He hates that Jackson’s has him bent over with his ass in the air while he holds himself open so that he can be stretched by his fingers; but despite the humiliating position, he somehow finds himself feeling more confident about himself than he has in a long time. Jackson wants Derek and isn’t shy or embarrassed by it, it may just be for his body but judging by the soft kisses, the slow prep and the teasing caresses, Derek would bet that Jackson feels privileged that Derek is sharing his body with him and that’s far more then anyone has given him in years. Though he still firmly believes Jackson is a little shit, it just means he might not punch him in his pretty face before he leaves.

Derek grunts when the second finger slides in but moans out loud when Jackson’s mouth wraps around one of his balls and gently sucks. He wishes his hands were free so he could cling to the covers, digging his nails into his ass would just help Jackson out with the prep work. Derek wonders if that was the point, Jackson seems to have a reason for everything he does.

Jackson’s fingers begin to scissor him open while Jackson mouth offers the other testicle the same treatment. Derek’s cock is already leaking and Derek really can’t remember the last time he’s been this turned on. Maybe back when he was dating Kate, months before his life fell apart.

Jackson removes his fingers from Derek’s hole and his mouth abandons where it had been massaging his balls with his tongue and lips. Derek whines at the loss and can’t even bring himself to care when he hears Jackson chuckling at him. Derek is slightly distracted by the sound of foil ripping and he peers between his legs to see what Jackson is doing. Derek had been sure Jackson was going to put the condom on and start fucking him, but is surprised when he notices the condom - still rolled up - resting between Jackson’s lips. Jackson takes hold of Derek’s weeping cock and pulls it back between his legs and angles it towards himself. Jackson ducks down a little since Derek’s hard cock won’t bend back quite far enough, yet someone manages to keep the condom from falling out his mouth. Derek watches transfixed by Jackson’s mouth as his lips wrap around the head of his cock and he pushes the condom down. Once Jackson’s mouth has the head of Derek’s cock fully engulfed he gently presses down with his teeth to force the condom up the rest of the way up Derek’s shaft. Derek groans at the erotic porn star move Jackson seems to have mastered and full out moans when Jackson’s lips reach the base of his cock without gagging. Derek’s been with a lot of men and knows his cock isn’t small and very few have been able to deep throat him and fewer still without gagging.

Jackson lets the cock slip from his lips and Derek feels it slap against his stomach, condom perfectly in place. Jackson gives Derek a cocky grin and Derek barely even wants to punch it off his face for it.

Since punching clients in the face is a poor decision to encourage repeat business Derek settles for saying, “I think one of us is in the wrong line of work.”

Jackson smirks before shoving three fingers back into Derek’s hole causing him to grunt at the intrusion. Jackson’s smirk widens.

“Considering one of us is a whore and the other is unemployed I’d say we both might want to consider different working arrangements.” At Jackson’s words Derek decides that Jackson is a bit of a paradox. He never bats an eye when he talks about Derek’s profession but actually looked embarrassed when admitting to his lack of employed.

Derek doesn’t have much time to think about it before Jackson grabs his cock again and wraps his lips around it and starts sucking. Derek hates being wrong, hates it with a passion. He never admitted to it to his sisters and chances are he’ll never admit it to Jackson, because Jackson already clearly thinks so highly of himself and Derek’s sure it wouldn’t be healthy for his ego; it might develop diabetes if it got any fatter. He’s not sure how he feels about the fingers in his ass but Jackson’s sucking skills are hands down the best he’s had to date. He’s never been sucked in this position, from behind, but the angle is forcing the sensitive head of his cock down onto Jackson’s tongue and Jackson’s sucking with the perfect amount of pressure and Derek doesn’t think he’s going to last long at all.

Jackson keeps sucking away while fucking his three fingers relentlessly into Derek’s ass. Derek’s not sure what he’s babbling about but knows its probably exactly what Jackson wanted, to reduce him into a wanton mess begging for release.

“Fuck, I’m gonna come.” Derek moans. Within an instant Jackson’s mouth is gone from Derek’s cock and Derek wants to cry at the loss. Only he doesn’t get a chance because Jackson’s fingers vanish from his hole and he rips off the condom and tosses it halfway across the room. Derek momentarily thinks of commenting on how gross that is, but then Jackson wraps his fingers around Derek’s cock and starts stroking him in long rapid motions from base to tip; his balls are lightly being smacked by Jackson’s wrist due to the backwards angle and somehow that just makes it better. The orgasm hits him hard and he can feel his come pulsing out of his cock, Derek’s vision blurs with such intensity that he has to close his eyes to collect himself while Jackson continues to stroke him through it. He’s sure he’d moaned out some garbled version of Jackson’s name but hopes it was inarticulate enough that Jackson didn’t notice.

Jackson keeps stroking his cock and Derek hisses when the oversensitivity kicks in and it becomes too much. He opens his eyes and peers back at Jackson who doesn’t even look smug like Derek had expected. Instead he’s fully concentrated on jerking Derek’s cock. He realizes that from their current positions with Derek practically on all fours with Jackson jerking him off while his cock hangs heavy between his legs, its somewhat reminiscent of someone milking a cow and Derek finds the whole thing somewhat embarrassing.

Derek notices Jackson’s left hand had collected the bulk of Derek’s release in his palm and Derek looks at it in confusion. Before Derek can comment on it Jackson stands up and grabs hold of his hard condom covered cock and strokes Derek’s come into it. He has no idea when Jackson managed to get the condom on, given his hands always seemed to be busy doing something fantastic to Derek’s body, but Derek can tell Jackson’s talented at multitasking. Instead he asks the more confusing question.

“Are you lubing yourself up with my come?” Derek’s asks in an incredulous tone. The idea of it sounds gross to Derek and cant believe the idea even game to Jackson.

“Um, yeah. Sorta?” Jackson responds and it’s the most unsure Derek’s heard him sound all night. Most shocking though is the blush that clearly spreads across his cheeks and he won’t meet Derek’s eyes. Clearly it’s a weird new kink of his that even he’s still working out. “That’s not a problem is it? I figured it would be fine since I’m wearing a condom and its kinda, yours after all.” And somehow the blush spreads even more and Derek can’t help but find it endearing. “Never mind. Its weird, I’ll just get another condom.”

“Its fine.” The words leave Derek’s mouth before he even realizes it but the more surprising part is that he finds he actually means them. Their whole night so far has been weird and Jackson pushed Derek into doing things he never would have done on his own; but for whatever reason enjoyed doing them. Plus Jackson is paying him far more than he normally charges, so maybe he can handle this for Jackson.

“Seriously?” Jackson sounds sceptical but hopeful too and when Derek nods and says sure, Jackson full on smiles. No smirk or grin but a genuine smile which leaves Derek longing for friends again. Manny had been the last one to give him a genuine smile, but that was just Manny, somehow every smile the boy gave came off as genuine.

“Um, thanks.” Jackson mumbles before taking up position behind Derek. “Spread your ass for me again.”

Derek’s not even surprised that Jackson’s back to normal after their awkward moment, he also can’t remember when he stopped holding himself open for Jackson. He assumes it was sometime during the mind blowing orgasm, but doesn’t argue and spreads himself open as requested.

“I was hoping to fuck you for a long time, nice and slowly. But given how fucking gorgeous you are and how hot you were while I sucked you off and stretched you open I’m probably going to last about as long as a fifteen year old boy getting to fuck his favourite porn star.” Jackson states as the head of his cock slowly breaches Derek’s entrance.

Derek grits his teeth at the intrusion and doesn’t voice that he considers Jackson’s admission to be good news. Now that he’s come and no longer has the distraction of Jackson blowing him he finds that he just fills uncomfortably full.

Jackson slowly inches forward until he finally bottoms out and Derek can feel Jackson’s balls resting against his ass. He stops moving and gives Derek time to adjust.

“You can do whatever you want with your hands now.” Jackson’s voice is a hoarse whisper inside in his ear and it sends shivers down his spine. Derek is relieved at the permission and quickly adjusts his position so he’s resting on his elbows. “Just a warning, I was purposely ignoring your prostate earlier while I was getting you ready.”

Derek planned on asking what Jackson was talking about but didn’t get passed the ‘wha’ before Jackson pulled out and slide home in one swift motion hitting his prostate at a perfect angle. Derek couldn’t hold back the appreciative groan if he had tried.

“Tell me to stop if I get carried away, I tend to do that sometimes.” It’s the only warning Jackson gives before he’s pulling out and thrusting back in at a ridiculously fast pace. Its intense and Derek silently curses all those past johns who didn’t take the time to show Derek just how good getting fucked could be. Derek finds himself planting his face back into the pillow and hugging it tight to muffle the embarrassing noises that were escaping his lips. The new angle with his ass in the air feels amazing and Derek can already feel his cock coming back to life with renewed interest. Jackson keeps pounding away and after a minute of awkward seemingly random thrusts he’s worked out the right angle that has Derek begging for more. He’ll never admit it to Jackson, luckily they won’t be in each others lives long enough anyway, but he’s glad he let Jackson lube himself up with his own come. Between the sounds of skin on skin and the raunchy dirty squishy sounds made every time Jackson thrusts his cock in Derek finds himself impossibly turned on again. He’s even loving the feel of Jackson’s balls slapping off his ass.

“Oh fuck.” Is the only warning Derek gets before Jackson pulls out of Derek and rips off the condom and jerks himself off over Derek’s back. With a groan Derek feels the warm splatter of several loads of come coating his back and just above his ass.

Derek doesn’t have long to morn the loss of Jackson’s cock when Jackson reaches between his thighs and begins stroking Derek in the same rough manner he had from the first time. Derek’s cock is sore now and he’s sure his balls will be too with how fast they’re bouncing off Jackson’s wrist, but he can’t bring himself to care when his second orgasm hits and he spends himself over Jackson’s knuckles and the quilt below.

Derek allows himself to slide forward onto his stomach and stretches out. It feels nice after being hunched over in the position Jackson ordered him into since getting onto the bed. For a moment Derek forgets this was a job and thinks of it as an amazing one nightstand. The kind where you want to ask the person out to coffee in hopes you get along because coming home to sex like that every night would be amazing. But then Jackson speaks and reality comes crashing back to him.

“Sorry, I think I got come in your hair.” Derek’s doubts he’s sorry at all because Jackson sounds more proud and a little smug of shooting that far. He doubly doubts his sincerity when he wipes Derek’s come onto his ass to clean his hand off. Its quiet for awhile before Jackson breaks the silence again. “You were fucking amazing.”

Derek’s not really sure why Jackson is giving him so much credit for how great the sex was because he feels like he just sat there and took orders while Jackson did all the work. He won’t voice that thought though, if he’s lucky Jackson will become a regular, Derek won’t complain about great sex that pays almost five times more than his current regulars.

Jackson jumps off the bed and disappears into the door he assumes leads to a bathroom, a few moments later he returns and Derek feels a cool damp cloth running down his back. It feels nice and Derek indulges in being the one taken care of for once. He even lets Jackson run the cloth down the cleft of his ass and down to his thighs. Derek rolls onto his side after Jackson finishes and takes in the mans debauched appearance. He’s tucked his cock back into his boxers but his fly is still down which makes Jackson have to hold them up with one hand to stop them from falling down. Jackson picks up the two wayward condoms and dumps them into a trash can in the corner and proceeds to buckle up his pants. Now that Derek looks back he realized that Jackson never actually got naked, kept his shirt and pants on the entire time. He wouldn’t have minded if he got a chance to see him naked, he’s sure his body is as sculpted as his face.

Jackson makes his way to the end table where the money was placed and scoops it up and pulls out his wallet. Derek is about to voice his confusion when he realizes Jackson is actually taking more bills out of his wallet. Jackson tucks his wallet into his back pocket and pulls something else out of his side one.

Jackson squats down at the side of the bed so that he’s near eye level with where Derek lies still naked. “You have two choices.” Jackson says as he holds up his hands to show Derek. “A thousand dollars for a fantastic night and you go on your way and we never see each other again,” Jackson holds up his right hand where a large wade of bills are enclosed. “Or this.” Jackson holds up a single key dangling from a large silver oval key chain with something kind of embroidery etched into the metal.

At Derek’s confused look Jackson explains. “It’s a key to the house. No rent, no bills, foods taken care of and the only condition is while you live under this roof you’re not allowed to use sex as currency. Not for money, favours or anything.”

Derek’s confusion vanishes and he goes straight to being pissed off. This isn’t some lame Hollywood movie and he’s definitely not Julia Roberts and things like that don’t actually happen in real life, not to someone like him. Taunting someone with an easy no strings attached life after surviving such a shit one for so long is just cruel.

“Fuck you and your fake charity.” Derek growls as he crawls off the bed and moves to snatch the wade of bills. Jackson quickly pulls them out of reach and Derek stands up ready to claim his money.

Jackson places both the money and the keys back onto the table and backs away with his hands up in some sort of a placating gesture.

“Don’t get all pissy, the offer is real.” Jackson says and Derek ignores him and grabs the money and starts picking up is cloths. “Look, don’t decide now, take the night to think it over. Shower, sleep and decide in the morning. If you want the money, fine take it and leave the key, if you would rather stop selling yourself for pathetically low amounts of money then keep the key and bring me back the money in the morning.”

“Why?” Derek asks venom still in his voice because he’s mad at himself for hoping this might be real and mad at Jackson for the stupid games he’s been playing all night.

“I have my reasons.” Is the only answer Jackson gives.

“That’s not good enough. If you want me to trust you that this is real I’m going to need more than that.” Derek demands.

“Well tough shit, that’s all you get. Stick around and maybe I’ll tell you but right now all I know is that you’re a whore with a hot ass and a real good lay.” Jackson shouts and then takes a moment to collect himself. “Look I get everything sounds too good to be true, I don’t blame you for that. I’m already expecting you to take the money and leave, its what most of the others have done. Just when you go don’t steal anything cause then I’ll have to send to cops after you and I think I’ve been pretty fair between the cash and the multiple orgasms and all.”

Derek huffs out a short laugh and shakes his head. “Can’t you give me something? Free room and bored sounds wonderful but I’m still waiting for the catch. Am I meant to be an easy lay? Keep me at home so you can fuck me whenever the mood strikes, were you once a prostitute too who found his own Richard Gear and now you go about paying it forward?”

“Why the hell do you people keep comparing me to Richard Gear?” Jackson asks.

“Seriously? You’ve never heard of Pretty Woman?” Derek asks and continues at Jackson’s confused look. “Stars Julia Roberts as an hooker, Richard Gear plays some rich dude who hires her to be his date and they fall in love and he saves her from a life of soliciting? It’s a classic, you had to have heard of it.”

“I don’t watch black and white films.” Jackson responds and when Derek realizes he’s not joking he’s shocked.

“Classic doesn’t mean black and white you idiot, its any movie that remains relatively popular over the years.” Derek doesn’t hide the exasperation he’s feeling.

“Fine whatever. I’m Richard Gear, and you’re Julia Roberts if that’s how you want to see it. Only you don’t have to date me, you don’t even have to fuck me. You can see whoever you want.” Jackson says.

“But I’m still not hearing the catch and I’d really like some sort of assurance that this is real.” Derek pleads because the more they talk the more he tricks himself into believe this is for real.

“Look, there is no catch unless you count the house rules, which are pretty simple. Rule one is use common sense and rule two is pretty much incorporated into rule one, but just like I had said earlier, no using sex as currency. You fuck whoever you want whenever you want, but only because you want to and not because you’re hungry. That includes me, the next time we fuck its going to be because you’re horny and can’t wait to have my cock buried balls deep in your ass again, not because you’re grateful for me putting a roof over your head.” Derek wanted to laugh in Jackson’s face and tell him to dream on but when his cock throbs in interest at Jackson’s words he thinks it better to just stay silent and listened. “Besides, I already have a permanent fuck…” Derek notices the way Jackson stutters over his words and blushes. Derek finds himself curious about who this mystery person is because he clearly has Jackson feeling insecure for some reason. “…Person.” Jackson settles on.

The room is quiet for awhile before Jackson lets out a sigh and adds, “as to why I want to help its because the two closest people in my life use to be whores.” Jackson falls silent again and won’t make eye contact with Derek. “They’re both incredibly smart and the nicest people you’ll ever meet.” Jackson pauses and seems to think over his last sentence. “Actually, one of them is nice and the others a bit of a bitch, but they’re both impossibly smart. They just had shit luck and no one to give them a chance. I got a fuck ton of money which I didn’t really earn and I get bored so I pick up whores and let them stay here. Generally they either stick around and keep me entertained or they take the cash and whatever else they can carry and run off.”

“But why me?” Derek can’t help but ask. Whoever those other two were sound like they’re pretty amazing people, Derek’s pretty average in the intelligence department and cant think of what attribute Jackson saw in him that thought him worth saving over all the other kids working the streets.

“You really think I have some magic formula for how I pick up my prostitutes? Seriously I don’t even get a say, my actions are ninety-five percent governed by my cock. I’m two for twelve for getting ripped off by the people I bring home, honestly I’m starting to mistrust my cocks decisions.” Jackson confesses.

“So your telling me that you picked me up with the plan to fuck me and offer me a home strictly on the bases of wanting to have sex with me?” Derek asks for clarity but is pretty sure he already knows the answer.

“Pretty much. Wasn’t even going to pick anyone up tonight but then you went and bent right over as I was driving by. My dick made it pretty clear I had no choice in the matter from then on.” Jackson’s smirking and Derek is sure its because he can see the heat Derek can feel rising in his cheeks.

“That wasn’t meant to be an advertisement.” Derek admits. “I had dropped something and was picking it up.”

“Whatever, it got me to notice you.” Jackson says as he covers a yawn. “I’m about to pass out so I’m going to head to bed. Shower, spend the night and think it over. I get its hard and you probably don’t trust me for shit, but the offer is real you should give it a try.” Derek doesn’t respond because as much as he wants to jump in and just say yes he can’t bring himself to trust it. Jackson pauses in the doorway before leaving and glances back at Derek. “You agreed to let me fuck you bareback for a mere five-hundred bucks because you were desperate for cash. If you’re so desperate you’d risk contracting HIV maybe we met at the right time.”

Jackson leaves and closes the door behind him and Derek collapses onto the bed still naked. Derek can’t really argue with Jackson’s final point, things have been steadily getting harder and he’s slowly been getting more and more desperate to keep a roof over his head. He’s not dumb, he’s getting older and johns are slowly losing interest and favouring the teenage looking kids. He’s already had to drop his prices a few times and Jackson showed him that his safe sex rules are becoming negotiable.

He doesn’t really believe in fate like Jackson had implied, but he thinks he’s just desperate enough to believe in dumb luck. Maybe Jackson is the years of backed up luck finally making its back-payments he’s owed since his life fell to shit so long ago. Maybe he’s to tired to decide tonight.

Derek tucks the money into his jeans beside the file and ignores the key for now and drags himself under the warmth of the covers. He a little sticky and more than a little sweaty but he’s to tired to care. He tosses seven or eight of the ridiculous amount of pillows onto the floor and curls up around the largest one and shuts his eyes. He’ll decide in the morning, tonight he’ll sleep in a comfortable bed and enjoy the sore throbs in his ass whenever he moves his hips reminding him of the nights activities. And if he pretends the pillow he’s wrapped around is 5’9” and has short blonde hair no one will know.

**Author's Note:**

> Wow, this chapter ended up way longer than I had originally planned. Please let me know what you all think, feedback is appreciated.


End file.
